


Jensen and his weird destiny

by orphan_account



Category: Supernatural RPF
Genre: Anal Sex, Bondage, Dry Orgasm, Enemas, Extremely Dubious Consent, Light Bondage, Multiple Orgasms, Orgasm Delay/Denial, Pets, Sex In A Cave, Tentacle Monsters, Tentacle Rape, Tentacle Sex, Tentacles
Language: English
Status: In-Progress
Published: 2014-06-23
Updated: 2014-07-05
Packaged: 2018-02-05 21:50:43
Rating: Not Rated
Warnings: Rape/Non-Con
Chapters: 4
Words: 6,996
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1833487
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>"He didn't see the inky blackness bubbling up and over the sides of the well, and he didn't hear the tendrils snaking over the ground towards him.</p><p>But he felt them.</p><p>A tendril snaked around his ankle, climbing up to his knee before Jensen had even realized what was happening."</p><p>Jensen is attacked by a tentacle monster while wearing panties and afterward he realizes that the monster wants to keep him forever as its personal toy.</p>
            </blockquote>





	1. The woods

It all started when Jensen went to the third annual Halloween party held at the old house in the woods. The family had lots of money, a huge house surrounded by creepy woods, and had thrown the best parties according to his friend that invited him.

The theme this year was Gender Bend.

That is how Jensen ended up at a party in the woods wearing a short skirt, high heels, a belly shirt, and heavy eye makeup. To complete the look, he had donned a pair of lacy black panties with pink ruffles, a matching bra, and garters with stockings. In his defense, all of his buddies were wearing similar, and in some cases, more extreme versions of the same outfit.

The dare was, run out into the woods and bring back a brick from the old abandoned well that was a ways into the trees. It was rumored to be haunted and therefore a popular choice for truth or day games.

So Jensen, slightly intoxicated, had run out into the woods. No one had followed from the house to make sure he did it, which was weird. But Jensen was determined to follow through.

The woods were dark and a chill was settling over the night air. It was past midnight, and the sounds of the forest were loud and unknown as the nocturnal creatures made their way out of hiding to find mates and feed. The thrumming of the music from the house was barely audible as he went deeper and deeper into the woods. He felt his buzz receding as he realized he wasn't quite sure where he was anymore, having lost his bearings as the drunk are prone to do. The sounds of nature suddenly seemed to die off, leaving him alone in the silence that was broken only by the beating of the bass.

Jensen turned, a cold feeling that had nothing to do with the temperature seeping into his skin. But right there was the old well, bricks crumbling and the hole yawning deep into the earth. Jensen sighed in relief. At least he knew where he was now. He approached the well with and reached out to take a brick. It broke off easily, sending a few small bits to fall down into the well. Jensen didn't hear them hit the bottom.

He turned to leave, brick clutched tightly in his hand. He didn't see the inky blackness bubbling up and over the sides of the well, and he didn't hear the tendrils snaking over the ground towards him.

But he felt them.

A tendril snaked around his ankle, climbing up to his knee before Jensen had even realized what was happening.

"The fuck..?" Jensen tried to shake of the tentacle. It was slender but gripped him with surprising force. Jensen started backing away, finally noticing the thickening ropes coming out of the well, seemingly with no end. They were black, but seemed to be glowing slightly, enough to be distinct amid the darkness of night. Jensen stumbled back, tripping in his heels. He fell hard onto his back, and the tentacles took their chance. The swarmed him all at once, grasping his wrists and his ankles, wrapping around his arms and legs and torso, completely immobilizing him. Jensen stayed perfectly still.

This couldn't be happening.

One wrapped around his mouth like duct tape, silencing any cries for help. The one that had originally twined around his ankle now made its way leisurely up the side of Jensen's leg, pausing once in a while to rub against the skin. It reached the hem of his skirt and played with it briefly, lifting it up and pushing it out of the way. Jensen shuddered as it rubbed at the length of his cock through the thin fabric, toying with the pink ruffles that adorned them.

Now Jensen was struggling. He had watch enough cartoon porn to know what was happening to him right now. He didn't know how it was possible or why it was happening to him, but there was no way he was going let this happen to him.

The tentacles had other ideas though. They lifted him gently off the ground, still immobilized. The tentacle investigating his panties was joined by another which pushed them to the side, freeing his half-hard cock. In Jensen's defense, the fabric of the panties had something to do with it as well as the tentacles' rubbing.

Suddenly, his skirt was forcibly ripped from his body, split and discarded somewhere out of sight. His shirt suffered the same fate, fluttering to the ground five feet below. Jensen struggled harder, left in only his lingerie, which was being thoroughly investigated by several tentacles. Two were under the bra, massaging and sucking on his nipples, bringing them to peak hardness while another toyed with the fastenings holding up his stockings. The tentacle in his groin resumed its exploration of his cock, trailing lower and lower towards his hole.

These were all the least of his concern however. The tentacle that had been acting as a gag receded and formed itself into a much more phallic shape. It tapped against Jensen's clenched lips, seeking entrance. Jensen shook his head furiously, keeping his lips shut. Seemingly annoyed by his response, the tentacle that had been moving towards his ass brushed lightly against his hole, smearing something cold and tingly against the sensitive spot. Lube. Jensen gasped involuntarily, allowing the tentacle at his mouth to thrust in all the way to the back of his throat in one movement.

Jensen choked and made a retching sound as the gelatinous substance filled every crevice of his mouth. It tasted like unflavored jello and was surprisingly warm. A sweet substance trickled down the back of his throat, causing Jensen to cough around the tentacle. He tried to cough it up, but there was nowhere for it to go and more of the stuff continued to pour down his throat. Jensen felt a warmth in the pit of his stomach as if he had just drank a strong liquor. It spread up his throat and out towards his extremities, one in particular. His cock, only half-hard until now, was suddenly painfully hard as if he had just taken a shitload of Viagra. So it was an aphrodisiac, Jensen realized with dread. He was horrified and repulsed even as he arched upwards to the tentacles sucking on his nipples, overcome by sensation.

Moans escaped around the thick tentacle in his mouth, which it seemed to like because it began pulsing, retracting and then pushing in again to his mouth. Jensen fought the urge to let his head fall back and allow the tentacle deeper.

He felt a pressure on his hole, one thin tentacle pushing gently at the ring of muscle. Jensen clenched. He was half naked and had a tentacle in his mouth but there was no way he was allowing this to happen. The tentacle seemed to have different ideas, pushing in anyways. It must have secreted more lube because Jensen felt cold liquid being pumped into him as the tentacle made its way into him. It dripped out of him when the tentacle starting pumping in and out, the burning pain receding and being replaced by an exquisite sensitivity. Jensen's nerve endings felt like they were on fire, even as his brain short-circuited on fear.

The tentacle in his mouth slipped further into his mouth and down his throat, increasing its pace until it was brutally fucking his throat and cutting off his air with every other thrust. Tears formed in Jensen's eyes, running down his face and smearing his makeup. His bra was ripped off, stinging the skin with the force at which it was removed. The tentacles sucking his nipples smeared pre-cum over the sensitive skin, reddened and puckered from their administrations.

Another tentacle joined the one fucking his ass, larger than the first, about the size of two fingers. Jensen felt himself push back on it with shame, his body's arousal overcoming his mind's revulsion. The two tentacles thrust in tandem, both moving together at the same pace. Jensen felt his legs lifted up and separated, his knees pushed back until they almost touched his ears. He groaned in pain as his muscles protested the stretching pain. He didn't bend like this! His was going to be injured!

His panicked thoughts were interrupted when both tentacles in his ass suddenly pulled out, splashing their release all over him. Jensen shuddered, sticky and shaking with his own arousal. His mind was too far gone with the need to cum as more of the sweet fluid poured down his throat and into his stomach. Jensen eagerly sucked on the tentacle, whining when the tentacle receded. Jensen didn't care anymore, he just needed to come. The sensations were overwhelming, his nipples still being played with, and his hole open and gaping with cum dripping off his body. Jensen was vaguely aware of being pulled towards the well when a new tentacle, thick and blue and pulsing with light slithered its way out of the well and towards him. It was huge, the thickness of his arm at least, and Jensen felt a thrill of gross excitement run straight to his cock.

When this tentacle breached him, it hurt.

A lot.

But more lube was pumped into him, and the pain retracted. This tentacle was different. It vibrated inside Jensen as it pushed inside, not thrusting but instead pushing in and in and in, tapering and thinning as it went further inside. Suddenly, his situation seemed far less unappealing, as if his mind was being made up for him. His skin felt like a thousand tiny sparks were dancing over it. Jensen moaned and bucked his hips, searching for release, begging around the tentacle in his mouth for whatever this monster was to just fuck him, go deeper inside. To let him come. He hoped no one found him like this, stuffed with a glowing tentacle, moaning and bucking like a cheap whore. Another tentacle pushed itself inside Jensen's mouth, stretching his lips around both as they fucked his mouth. Jensen tipped his head back to allow them better access, and tried to pull his legs back further in an invitation even as self-loathing bubbled in the recesses of his mind. A thin tentacle took him up on the offer, poking at his stretched rim and working its way inside until it found his prostate. It started  _sucking_ on it, and Jensen screamed as his vision went white and his legs went numb. He vaguely felt the tentacle in his mouth pull out and spill hot cum all over his mouth, face, and stomach.

When Jensen woke, he was lying on the cold ground in complete darkness. He was sticky with his own release and that of the monster that had violated him, his muscles sore and lethargic. He didn't want to move. It was silent save for the dripping of water. He was underground. He wondered what time it was, if anyone was looking for him after he didn't come back from his dare. He was wearing only his panties, the rest of his clothes lost. It didn't particularly matter

And there was still a tentacle in his mouth, so deep down his throat he swore he could feel it in his stomach. The weird thing was, he didn't feel suffocated like he should. He had the strangest feeling of belonging, like he was where he was supposed to be, like he was supposed to spend eternity as a fucktoy with a tentacle down his mouth. Part of him felt horrified at the thought of "belonging" with a tentacle down his throat in a cave. But the rest of him had accepted it.

In the darkness, he saw a light coming towards him, a blue light.


	2. Jensen gets an enema

Jensen watched the blue tentacle approach him, too exhausted to do anything. Strangely enough, he felt no need to run, or try to get away. As if that wasn't weird enough, he started getting hard.

_ You're mine. _

Jensen more felt the voice in his head than he heard it. He tried to respond, but the tentacle down his throat stopped him. This thing felt...old. Ancient, even. And so, so evil. Jensen wondered if it was going to kill him.

_ You were so beautiful, I knew I had to have you. And now you will stay with me until I decide to let you go. You will not age, you will not die, and you will want for nothing. _

Jensen felt panic welling up inside him now. The part of him that was terrified was growing stronger now that he was faced with actually staying with this thing. As if sensing this, the blue tentacle reached out and nuzzled Jensen's face. It left a trail of ooze that sent a tingling feeling through Jensen's skin. He swallowed nervously around the tentacle filling his mouth, and noticed something. He wasn't hungry. He hadn't eaten in hours and had been intensely fucked. He should be starving. But he wasn't.

_ I will provide for you, and in return you will provide for me. _

Jensen wanted to point out that he hadn't asked to be provided for, but a nosy little tentacle was toying with the seams of his panties. It pushed under the edge and cupped his balls, stroking them gently. Jensen moaned as he got harder, his erection peeking out from under the panties. Two more aligned themselves under the seams, and in one motion pulled them down to his ankles. Cold air ghosted over his erect cock and Jensen shuddered. His wrists were bound behind his back and he let himself be maneuvered into a position with his face in the dirt and his ass in the air. Bits of stone dug themselves into Jensen's knees until he was lifted once more into the air. He writhed with pleasure as a tentacle pumped him expertly, humping down into the thing's touch. His legs were bent so that his heels touched the bottom of his ass, and his thighs were being held apart.

Jensen relaxed into the tentacles' hold. He didn't want them to drop him. and honestly, now that his body was awake, it was definitely interested in being fucked again. He didn't know how he could possibly be ready for round two so quickly, but as the tentacle in his mouth fed him more sweet syrup and the aphrodisiac took effect, there was no doubt in his mind that he was ready.

The first tentacle that pushed into his hole this time was small, about the width of his middle finger. It felt good, but he was still loose from the first time so it didn't fill him. Another soon joined it though, both secreting lube. Loud squelching sound filled the air as he was filled with too much lube and the tentacles fucked in and out, nailing his prostate.

Jensen's moans were rising in pitch as the tentacle pumping his dick sped up and match time with the furious pace of the ones in his ass. He was on the edge of cumming within minutes, and when the first tentacle in his ass creamed inside him and sent cum dripping down his legs, Jensen exploded with thick ropes of cum. He thought he was done, but another two tentacles replaced the one that had pulled out. Jensen shook from the friction in his over-sensitive body, his dick still being pumped. He screamed and pleaded around the tentacle in his his mouth, and another pushed its way past his teeth.

_ Beautiful. So open to me. _

Jensen would have rolled his eyes but he was so overwhelmed that he barely heard the monster speak. His orgasm left his trembling and yet he was still desperately rutting against the tentacles inside him and sucking on the ones in his mouth. More tentacles found their way inside Jensen, tickling over his prostate and squirming past, deeper and deeper, squirting lubes they went. It was too much, the lube was filling him, his belly was swelling and cramps wracked his frame. The tentacles retreated slowly one by one until only one was left, the thickest one, and it swelled inside him until it formed a perfect plug, sealing in the lube.

_ Very impressive. A full gallon. _

Realization hit him like a ton of bricks.

He was getting an enema.

He jerked and twisted with cramps, his belly distended and hard, and tentacles stroked and caressed it, pressing in to make him gurgle wetly around the tentacles in his mouth. More sickly sweet liquid was pumped into his stomach until he was too full, bloated and squirming and _full_ to the point where he felt like he might explode.

New tears formed. He felt like he needed to throw up, and shit himself, and he needed to _cum_ even though he hadn't even noticed himself becoming hard.

This is how he stayed for he didn't know how long.

Suspended off the ground with his panties around his ankles and ass in the air. A tentacle plugging a gallon of lube inside his ass and still sucking desperately at the tentacle in his mouth to get still more of the sweet stuff into his already full stomach. It spilled out from between his lips and dribbled down his chin, and he wondered in a brief moment of clarity if it was the same lube that was filling him. He felt the panties lifted off of his feet and a thrill of excitement ran through him at the thought of being completely naked in the sight of this terrible beast. This ancient presence that was at the moment fondling his swollen belly, pushing and prodding it to make him gurgle around the tentacles in his mouth.

A sharp sting to his buttocks made Jensen thrash. Another sting, and another followed. The tentacles were whipping him! Jensen felt his gag reflex come back in full force, choking violently around the smooth surface. How could he not? It felt like it was all the way in his stomach.

_ You look so perfect like this. You were meant for this. _

Jensen didn't know how long he was kept this way, but his dick never softened, an effect of the aphrodisiac in the lube. His squirming quieted, and only his moans could be heard when a cramp made him tremble. Tentacles drifted over his skin, tweaking his nipples, massaging the skin between his thighs, even running through his hair.

Suddenly, Jensen felt himself moved so he was facing what he assumed was the ceiling of the cave and his ass, stuffed with the tentacle, was facing the ground. Numerous tentacles supported his weight easily. The tentacle plugging pulled out slowly, and he sighed as he finally evacuated all of the liquid. It dripped and splashed onto the ground below him and Jensen felt a mini-orgasm sweep over him just at the feeling. A rumbling in his stomach and the tentacles in his throat started sucking up the excess fluid in his stomach, and when they were finished they retreated until they popped free of his mouth. Jensen whimpered and tried to follow them with his lips, only to be stopped by his restraints. He was laid gently on the ground, and he suddenly felt bone tired. His eyes fought to stay open though.

"Please..." Jensen whispered, his voice wrecked and raspy. "I need..."

_ I knew you were special. _

Jensen sighed happily as his mouth was again filled with a tentacle. He didn't like being empty.


	3. Jensen has tentacles all up in him

There were rarely times when Jensen wasn't plugged in one hole or the other or both. It felt normal to him, familiar even. He lost track of time after the first few days, but he was relatively sure he was fucked or generally molested at least once a day.

Jensen's eyes were much more accustomed to the darkness now, and he could make out the shapes of the tentacle in his mouth trailing down his chest and leading off into the dark. More tentacles were moving towards him and Jensen reached out for them with his hands. They swarmed over him, rubbing and nuzzling at his body, twirling around his nipples and suckling his neck. Jensen leaned into their touch and trailed his hands over the ones he could catch. They were soft and a little bit slimy as they twirled around his fingers and traveled up his arms. Jensen felt the first tentacle slipping down between his ass cheeks towards his hole.

God, did this thing ever get tired of fucking? Because Jensen was pretty sure that's what was about to happen again.

It slipped inside easily and began to thrust gently, almost like it was exploring him.

_Such interesting creatures, humans. I've wanted to know how you...operate._

Jensen's eyes widened as he felt the tentacle push in further than it had ever gone, only stopping when Jensen began to wriggle in pain. He shook his head frantically. It couldn't go any further, it just couldn't! Jensen tried to tell the monster that a tentacle couldn't possibly go any further, that it was impossible and he couldn't take it. Thankfully, it retreated before it caused any damage, pulling out completely with a wet pop.

Jensen whimpered around the tentacle in his mouth, his hole clenching around nothing. He moaned around the tentacle in his mouth, which proceeded to pass down his throat until it felt like it was in his stomach, twisting and turning. The tentacle that had just been in his ass poked against Jensen's lips, slipping between his teeth. Jensen gagged as he taste himself along with the sweet lube that was being secreted. This tentacle contented itself with fucking his mouth lazily, sucking on his tongue and rolling around in what space it could find. His head was bent down to look at his stomach and with a jolt of fear, noticed something moving inside of his stomach. The first tentacle was actually inside of his stomach, wriggling around with zeal.

Two tentacles poked into his loose hole, stretching and massaging his rim. Jensen spread his legs further, urging them in deeper. But they didn't move in, content to just play with him, and more joined in on the assplay. Jensen moved to place his head in his hands in the dirt, ass in the air, legs spread and hole presented. The ass play seemed to go on forever, and when Jensen snuck a peek past his squirming belly between his legs, he saw seven tentacles holding his asscheeks open and stretching him. When they finally pulled away, Jensen tried to clench. He felt wide and open and wondered if he would ever be able to close again.

The tentacles in his mouth also retreated, tickling him as they danced over his tongue before sliding out all the way. Jensen looked up in the direction the tentacles were coming from, trying to see into the gloom while resisting the urge to rub himself against anything including the ground to get release. He felt something pressing at his slackened rim.

It felt like one huge tentacle at first, but in reality was five tentacles twisted together to form one large mass. Jensen pushed back on it, easing himself backwards slowly. Apparently unsatisfied with his pace, the column of flesh thrust inside him in one motion. It stopped at his prostate, giving Jensen flashes of pleasure with each tiny movement. Even with the slight stimulation, Jensen's eyes watered from pain and he cried out, all of the prep still not enough to make taking such a large object easy. It rolled in and out of him leisurely a few times, stretching and filling him with slippery lube before settling over his prostate.

"What...what are you?" Jensen croaked.

_I suppose you would call me a demon._

"Are you...going to kill me?" Jensen asked quietly, voice hitching halfway through the sentence as the tentacles inside him massaged his walls. The blue glowing tentacle merely retreated into the darkness. Jensen felt his heartbeat speed up. He was going to die down here, wasn't he?

A wave of survival instinct slammed into him, cutting through the haze in his mind for a moment, long enough for Jensen to start struggling, clawing at the ground and trying to get away.

The result was instantaneous. His wrists were caught by several strong grips and he was hauled up and off the column of tentacles, leaving him clenching his loose hole uselessly on nothing. He cried out as his shoulders were wrenched painfully. He tried to apologize, he really did, but his mouth was filled with a tentacle before he could form the words. Tears pricked at his eyes at the harsh treatment. A thin tentacle slipped up his leg and wrapped around the base of his cock, cutting off any hope of release. He was placed back on the ground gently, but he was placed on his hands and knees and restrained in that position.

_I see you need to be reminded of your place._

Jensen shook his head. No, he didn't! It wouldn't happen again!

But it was worthless. The tentacles in his mouth squirted fluid into him, increasing his already desperate state. Something slithered up his leg.

It felt like a big, slow slug. It was short compared to the tentacles, maybe ten inches long, and impossibly wide. Two tentacles pulled apart his cheeks, smearing fresh lube over his wide hole and pulling lightly at the rim, playing with him. The thing sliding up his leg nudged in, pushing further and further in without giving Jensen time to adjust to this new intrusion, wide even after all the prep. It kept going, stretching him to the point where Jensen was certain he would tear, a living, squirming dildo jamming itself inside him. When it finally was seated inside him, Jensen felt a tentacle wrap around his neck firmly, but not choking him, and he was pulled forward.

A leash.

Each movement caused the living dildo to move inside him, tickling and nudging his prostate, fleeting intense flashes of sensation that nearly made his knees go out. The tentacle around his neck pulled at him insistently, showing him who was dominant, leading him around like a prize pig. His dick was painfully hard, still trapped by the small living cockring. Just when Jensen thought he was becoming desensitized to the feeling, freezing cold lube squirted out of the thing inside him. Jensen's hips bucked with shock and he wailed, trying to stop. But his leash tightened to the point of cutting off some of his air and it continued to lead him around. Jensen whimpered, tears pricking at his eyes. He was being humiliated. It should be horrifying, and yet he was rock hard and willing to rub himself on anything just to cum. Not like that was an option though.

The cold feeling switched to hot, and Jensen's eyes rolled back in his head, his ass clenching uselessly around his squirming dildo as shocks that would have been his orgasm washed through him. Just as quickly, he was filled with cold again. Some of this cold lube dripped out of him and ran down his cleft and onto his cock, making him jerk and gasp and choke. A tentacle caressed his balls, full and heavy with their denied release.

The leash released his neck at the same as the living dildo pulled itself out of Jensen and slithered away to wherever it had come from. Jensen collapsed on the ground, shaking and moaning around the tentacles in his mouth. He felt something slide up his legs, something soft and fabric, and it took his fucked-out mind a minute to figure out that the tentacles were putting panties on him. They felt different from the ones he had been wearing. His reached a hand down to stroke them. They had a little bow on the satin front, and what felt like lacy ruffles down the back where they covered his ass. The fabric was already getting wet with the lube dripping out of him and the precome from his trapped cock. It never really occurred to him to ask where the monster had found such things, but then again, in this situation the fact that a  _tentacle monster_  had extra panties lying around wasn't the most unbelievable thing.

Jensen was raised off the ground again and pushed against the wall of the cave. Two tentacles rubbed his ruffle-cover ass, squeezing the fleshy globes with a painful amount of force. His dick scraped painfully against the stone wall, still hard and weeping, but unable to come. Jensen started grinding into the wall slightly, desperate for stimulation of any kind, ignoring the fact that he would probably have fabric burn on his dick. He felt the tentacle around his dick loosen.

_Rip_

A cool breeze brushed his ass through the hole that had just been torn into the panties. He came right then and there, screaming as he released pulse after pulse of seed into the panties (which he had a sneaking suspicion were pink), and the fabric stuck damply to him. Jensen shuddered, gulping down more sweet syrup from the tentacles in his mouth. Through the blissful haze of his orgasm, he felt a large tentacle pushing at the hole in the panties, ticking him rim. Jensen pushed back even as the over-sensitized skin screamed at him to stop. It pushed in without resistance, and was soon joined by another, and another, and Jensen lost track after five. They just seemed to keep coming. Two grabbed his writs and held them over his head, and two more secured his ankles so his legs were held far apart. The tentacles in his ass fucked him without rhyme or reason, each jostling the others to get further inside him, stimulating his prostate and squirting lube until it began to feel like another enema. Jensen moaned wantonly and keened when a particularly bold tentacle started jacking him off, pulling at his limp post-orgasm cock until it hardened. Jensen was over being shocked at his shortened refractory period. The panties were pushed aside, stretched over the tentacles and soaked with fluid. Jensen was pulled away from the wall and up into the air, still being fucked by numerous tentacles. He was being stretched further than he ever had before, and as a tentacle held his head up, he watched in fascination as a huge mass of tentacles moved in and out of him. Suddenly, he felt something new, something that was not pleasant. Some of the tentacles were pushing past where they should be able to push into him, past where they had stopped earlier. Jensen screamed around the tentacles in his mouth, cut off as they rammed themselves down his throat. The tentacles stopped thrusting and were only pushing in, in, in, further in. Suddenly the pain stopped and Jensen blacked out at the feeling of tentacles making their way through his body to his stomach. When he awoke, his stomach was wriggling and moving with many tentacles. Several extremely thin ones had forced their way into his mouth and down his throat. He panicked. How was he breathing? How could he survive having his entire body full of tentacles?

_You will not be harmed. You would not understand even if I explained, so I will only say that I am using magic._

Jensen calmed almost instantly. It was strange, he knew, to not be scared, but certainly this beast knew a thing or two about magic.

A tentacle returned to his cock, pulling at it until he began to harden. Jensen started to cry. He was so tired.

_We're just getting started._


	4. Experimenting with human intercourse

_We're just getting started._

Jensen shuddered, overcome with sensations that weren't entirely pleasant. He ran his hands down his stomach, and risked reaching under himself to feel the mass of tentacles stretching his hole. The column of writhing tentacles that led into him felt too big to possibly be inside him, though Jensen wasn't sure he was completely conscious. He felt a thin tentacle, much thinner than most of the others, trail down his stomach until it reached his dick. It stroked him, trailing lube over the head and stroking him to hardness, enhanced by the aphrodisiac in the lube. Jensen moaned low in his throat as it began peppering feather-light touches over his slit, almost like kisses, shaking as his body tried to cope with all of the intrusions. The thin tentacle poked into his slit, giving him time to adjust as it filled Jensen in a way that he had never been filled before. He thrashed weakly, held in place by his own exhaustion and the tentacles that grabbed his wrists, pinning them over his head.

Jensen was coated in a fine sheen of sweat as his his last hole was fucked slowly. The tentacle squirted lube as it picked up speed, and it spurted out of his dick with each thrust. It was too much for Jensen, and his muscles turned to jelly as his last intelligent thoughts melted away to be replaced by pure sensation. He felt something wrap once more around his base, effectively cutting him off from cumming again.

It felt good to be so full, the sense of being completely and truly owned. His dick throbbed with each thrust that wasn't quite enough to make him come and the tentacles inside his stomach wriggled with zeal for a moment before stilling, sitting motionless inside of him. The ruffled panties were misshapen and stretched around the tentacles in his ass and pushed aside by the one in his dick, and they were soaked to the point of dripping with lube and cum. It dripped obscenely down his legs and onto the ground below.

Jensen was like that for a long time, zoned out with every orifice plugged by slippery tentacles. His gag reflex would occasionally kick in, making him choke around the tentacles in his mouth, but he didn't mind. He found it strangely erotic when he choked, whatever that meant. He had never been much for submission in his life before this, but now it seemed like the only way to live was with this monster taking what he wanted while Jensen just took it like a bitch.

Finally, after what felt like hours, the tentacles began to move. They pulled out slowly, teasing his insides as they went, and when the first tentacle popped out it sprayed him with cum, splashing his ass and balls. He felt tingly and hollow as the tentacles started pulling out completely, one by one, each splashing their release onto Jensen until he was covered in it and more tentacles were still inside him. Jensen began to roll his hips weakly, trying to find his orgasm even as the tentacle in his dick began to pick its pace and the living cockring squeezed his dick tightly. He humped the air, trying to get it to go deeper, or get the remaining tentacles in his ass to fuck him.

They fulfilled his silent pleas, and the tentacles that had not yet left his ass started pumping in and out with a speed that he had never experienced. It felt like he would be torn in half by the force, each thrust of the fleshy mass striking his prostate with enough force to bring tears to Jensen's eyes. It hurt with the kind of pleasure that he was used to feeling when he was fucked roughly. He screamed as the tentacles in his mouth popped out, an animalistic sound that reverberated off the cave walls. The tentacle fucking his dick suddenly came, filling his dick to overflow with cum. Jensen's hips jerked upward on their own accord at the loss of stimulation, even as the back part of his brain registered how strange it felt to have spunk in his dick. The tentacle around his dick loosened suddenly, and it seized the front of the panties and began pulling them up and down by the waist band to make the fabric rub against his sensitive dick. Jensen gasped and struggled at the feeling of damp fabric rubbing him, but it wasn't enough to make him orgasm. The tentacles in his ass slowed to match the rhythm of the panties and Jensen writhed in agonized pleasure.

Another strike at his prostate had him orgasming, but no cum came out of his dick. With a bone deep tremor he realized that he was cumming dry for the first time. Maybe he had used up all of his seed. He felt himself dropped unceremoniously to the ground, hitting with a hard thud. The pain registered in his mind, but it was unimportant. The last tentacles pulled out of him as he fell, spraying their spunk on him from above, coating him with the substance as he lay twitching through the aftershocks of his release.

He lay there panting for a few moments, panties clinging wetly to him, wide-open hole fluttering uselessly. He swallowed around nothing as his throat was no longer filled with its usual tentacles. The slippery flesh of his dick was over sensitized and he was exhausted. But his rest was a long ways off.  
A figure loomed over him.

A human figure. Jensen moaned and tried to back away, dirt sticking to the tacky cum all over him.

"Hush, my pet. I have inhabited this body temporarily to experience how human...intercourse feels." Jensen calmed. The thing did say it was a demon. The man it had possessed had a deep voice, and it seemed fitting for such an ancient being to speak through it.

The man was tall, taller than Jensen. In the darkness, it was hard to make any defining features of his face, but Jensen wasn't trying that hard. He was still shaking and gasping from his earlier activities.

"I don't know your name." Jensen whispered, his voice raw and rough. He was tired of not having a name for this creature. The man cocked his head to the side and considered the question. Then he knelt between Jensen's legs and palmed his dick through the panties.

"You cannot pronounce my true name, nor should you. You may call me Master."

Jensen nodded, grateful for the name. His breathing hitched as the hand on his dick grabbed his balls and rolled them around nimble fingers. He wasn't ready for more, and his dick refused to get hard so soon after his orgasm without the lube. Master grabbed the front of his panties and pulled up, making them ride up his ass like a thong and rub against his dick in an imitation of what the tentacle had done earlier. He did this again, enjoying the way Jensen mewled in discomfort as the slippery flesh of his cock was overstimulated. Jensen blushed at the pitiful sound, but Master just stroked his face gently before sinking two fingers into his hole through the tear in the panties. Jensen shivered. It was so much more intimate to have a man finger fucking him than tentacles.

"I don't think you need any more preparations." He ripped the panties down the seams, smiling softly as Jensen squeaked at the action. He balled the panties up and pressed them into Jensen's mouth. Jensen let them sit there, a mixture of his cum and the tentacle cum mixed with lube coating his tongue.

Master freed his human cock from the clothes his vessel was wearing. It looked like it was big for a human male. His stroked it, marveling at how it was already hard. He pushed his girth slowly into his pet's red, puffy hole, enjoying the familiar heat. But it was different this way. Slower.

He slid the rest of the way in quickly, making Jensen's back arch up off the ground. He took Jensen's legs and pushed them back until they were almost by his ears, thrusting experimentally. His balls slapped at Jensen's ass and Jensen twitched and spasmed as his post-orgasm body was further abused. His cock refused to react, but that didn't affect Master. It was about what he wanted. Jensen's eyes rolled back in his head as he was jerked around by the thrusts. The possessed man seemed to have more stamina than an average person and he kept fucking Jensen for what felt like hours. Slapping sounds filled the air as Master played with Jensen's flaccid cock, enjoying the way Jensen trembled with too much stimulation.

Jensen groaned and begged weakly around the panties in his mouth for it to stop, to let him sleep. Finally, as Jensen was floating between conscious and unconscious, he felt the dick in his ass spill hot cum deep into him and stop buried to the hilt. It pumped seed deep inside him, coating his insides until it dripped out around his dick. Jensen tried to clench around the dick inside him, but he was too loose to do much to stop the man from pulling his now limp dick out of his hole. His legs were released and he let them flop to the floor boneless.

"That was fascinating, pet."

Jensen felt fingers tracing patterns on his sticky skin, smearing the tentacle cum and sweat and whatever else was there all over his body until he was completely painted with it. He felt so dirty, and tried briefly to remember what taking a shower was like. But that memory seemed to be gone along with many others. It was harder and harder for him to remember a life besides this one of constant stimulation and plugged holes. The man walked away into the darkness and Jensen whimpered after him. He was so empty.

Then everything went dark.


End file.
